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2-Naphthalenesulfonyl chloride → N-(2-{[(3-Hydroxypropyl)amino]methyl}-3,4-dihydro-2H-chromen-7-yl)naphthalene-2-sulfonamide

HRID 49462
Notes
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Reaction equation

HRID 49462 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:12]O)[O:9]2)=[CH:4][CH:3]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24](Cl)(=[O:26])=[O:25].[NH2:28][CH2:29][CH2:30][CH2:31][OH:32]>N1C=CC=CC=1.O>[OH:32][CH2:31][CH2:30][CH2:29][NH:28][CH2:12][CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([NH:1][S:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)(=[O:26])=[O:25])=[CH:3][CH:4]=2)[O:9]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 90863-Amino-1-propanolHCID 10511549(7-Aminochroman-2-yl)methanol

Product 1

HCID 10202719N-(2-{[(3-Hydroxypropyl)amino]methyl}-3,4-dihydro-2H-chromen-7-yl)naphthalene-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 1049
Pyridine
Solvent

Conditions

Temperature
80 °C

Procedure

A solution of (7-amino-3,4-dihydro-2H-chromen-2-yl)methanol (25 mg, 140 μmol) in pyridine is treated with 2-naphthalenesulfonylchloride (70 mg, 308 μmol) at ambient temperature for 1 h, treated with 3-amino-1-propanol (3 mmol, 0.23 mL), heated at 80° C. for 3 h, diluted with water and extracted with ethyl acetate. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue is purified by reverse phase preparative HPLC to give the title product, M+H 427, retention time 7.92 min.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-b252316eb42d4f76a074015cae6cf308
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06706757B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes